2-Methylsuccinic acid: Difference between revisions
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| PIN = Methylbutanedioic acid |
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| OtherNames = Pyrotartaric acid; 2- |
| OtherNames = Pyrotartaric acid; 2-Methylbutanedioic acid; Propane-1,2-dicarboxylic acid |
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| CASNo = 498-21-5 |
| CASNo = 498-21-5 |
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'''2-Methylsuccinic acid''' is an [[organic compound]] with the formula HO<sub>2</sub>CCH(CH<sub>3</sub>)CH<sub>2</sub>CO<sub>2</sub>H. A white solid, it is the simplest [[chiral]] [[dicarboxylic acid]]. It is a recurring component of urban aerosols.<ref>{{cite journal|title=Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere| |
'''2-Methylsuccinic acid''' is an [[organic compound]] with the formula HO<sub>2</sub>CCH(CH<sub>3</sub>)CH<sub>2</sub>CO<sub>2</sub>H. A white solid, it is the simplest [[chiral]] [[dicarboxylic acid]]. It is a recurring component of urban aerosols.<ref>{{cite journal|title=Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere|author1=Kawamura, Kimitaka |author2=Ikushima, Kouichi|journal=Environmental Science and Technology|year=1993|volume=27|issue=10 |pages=2227–35|doi=10.1021/es00047a033|bibcode=1993EnST...27.2227K }}</ref> Salts and esters of 2-methylsuccinic acid are called '''2-methylsuccinates'''. |
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==Preparation== |
==Preparation== |
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It can be prepared by partial [[hydrogenation]] of [[itaconic acid]] over [[Raney nickel]].<ref>{{cite journal|title=3-Methylthiophene| |
It can be prepared by partial [[hydrogenation]] of [[itaconic acid]] over [[Raney nickel]].<ref>{{cite journal|title=3-Methylthiophene|author1=R. F. Feldkamp |author2=B. F. Tullar|journal=Org. Synth.|year=1954 |volume=34|page=73|doi=10.15227/orgsyn.034.0073}}</ref> Alternatively, [[hydrocyanation]] of ethyl [[crotonate]] affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and [[nitrile]] substituents.<ref>{{cite journal|journal=Org. Synth.|year=1946|volume=26|page=54|doi=10.15227/orgsyn.026.0054|title=Methylsuccinic acid|author=George Bosworth Brown}}</ref> |
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==References== |
==References== |
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{{DEFAULTSORT:Methylsuccinic acid, 2-}} |
{{DEFAULTSORT:Methylsuccinic acid, 2-}} |
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[[Category:Dicarboxylic acids]] |
[[Category:Dicarboxylic acids]] |
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[[Category:Succinates]] |
Latest revision as of 22:11, 22 February 2024
Names | |
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Preferred IUPAC name
Methylbutanedioic acid | |
Other names
Pyrotartaric acid; 2-Methylbutanedioic acid; Propane-1,2-dicarboxylic acid
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.007.144 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C5H8O4 | |
Molar mass | 132.115 g·mol−1 |
Appearance | White solid |
Melting point | 117.5 °C (243.5 °F; 390.6 K) |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Methylsuccinic acid is an organic compound with the formula HO2CCH(CH3)CH2CO2H. A white solid, it is the simplest chiral dicarboxylic acid. It is a recurring component of urban aerosols.[1] Salts and esters of 2-methylsuccinic acid are called 2-methylsuccinates.
Preparation[edit]
It can be prepared by partial hydrogenation of itaconic acid over Raney nickel.[2] Alternatively, hydrocyanation of ethyl crotonate affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and nitrile substituents.[3]
References[edit]
- ^ Kawamura, Kimitaka; Ikushima, Kouichi (1993). "Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere". Environmental Science and Technology. 27 (10): 2227–35. Bibcode:1993EnST...27.2227K. doi:10.1021/es00047a033.
- ^ R. F. Feldkamp; B. F. Tullar (1954). "3-Methylthiophene". Org. Synth. 34: 73. doi:10.15227/orgsyn.034.0073.
- ^ George Bosworth Brown (1946). "Methylsuccinic acid". Org. Synth. 26: 54. doi:10.15227/orgsyn.026.0054.